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The Sixteen Year Old Virgin (2010)

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Despite being grounded, Jenny continues to secretly see Damien who tells Jenny that he wants to have sex with her. Meanwhile, Lily tells Rufus the big secret she has been keeping from him even though she knows it's a huge risk. Dan and Vanessa explore a new stage of their romantic relationship. Serena and Nate have an argument about their past events. Also, Chuck is forced to make an extremely difficult decision about transferring ownership of his hotel to Elizabeth when a lawsuit is served against him by female employees for sexual harassment and his devious uncle, Jack Bass returns to New York with an agenda.
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Title comes from the 2005 film The 40-Year-Old Virgin.

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Whole or part of the information contained in this card come from the Wikipedia article "Gossip Girl (season 3)", licensed under CC-BY-SA full list of contributors here.